When I fly out of Boston, anytime after late Oct, I always fly in jeans, turtleneck with a fleece pullover on top of that. Then, I carry my flannel lined windbreaker with me. On my feet are a pair of heavyish socks (Ragg type) and my Crocs. As soon as I get to my resort, I start peeling off clothing. However, I have my jeans, turtleneck and fleece pullover/windbreaker for those chilly evenings and I haven't used up a lot of valuable space in my bags. I pack a few more socks, a sweatshirt, short sleeved tees, and some shorts.
I think this a great idea! I plan on packing mostly jeans, short sleeve t-shirts with pull-overs/hoodies to go over them for mornings/evenings. I also will pack a few pairs of shorts and capris. I have a great fleece jacket from Land's End that is water repellant and is warm enough for anything above 40 degrees. If it gets colder, I'll layer a sweatshirt underneath it.
